7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid

Base Information

• Chemical Name: 7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid
• CAS No.: 136790-76-6
• Molecular Formula: C20H32F2O5
• Molecular Weight: 390.468
• Hs Code.: 2918990090
• European Community (EC) Number: 603-977-7
• Mol file: 136790-76-6.mol

Synonyms:136790-76-6;7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid;SCHEMBL454016;CHEBI:34945;WGFOBBZOWHGYQH-DKYLXPRQSA-N;AKOS015896617;1263283-38-0;7-((2R,4aR,5S,7aR)-rel-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoic acid

Chemical Property of 7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.49E-13mmHg at 25°C
• Melting Point: 56-59 °C
• Refractive Index: 1.486
• Boiling Point: 548.169 °C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 299.385 °C
• PSA: 83.83000
• Density: 1.052 g/cm³
• LogP: 4.30990
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 390.22178044
• Heavy Atom Count: 27
• Complexity: 525

Purity/Quality:

99% ^*data from raw suppliers

Lubiprostone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C1(CCC2C(O1)CC(=O)C2CCCCCCC(=O)O)O)(F)F
• Isomeric SMILES: CCCCC([C@]1(CC[C@H]2[C@H](O1)CC(=O)[C@H]2CCCCCCC(=O)O)O)(F)F
• Recent EU Clinical Trials: A Multicentre, Long-term Safety, Efficacy and Pharmacokinetics Study of Lubiprostone in Paediatric Subjects Aged ≥6 to <18 years with Functional Constipation
• Drug Interactions: Diphenylheptane opioids such as methadone have been highlighted in non-clinical studies to minimize the activation of CIC-2 depending on the Lubiprostone doses present in the gastrointestinal tract. The efficiency of Lubiprostone may be reduced if the patient is on concurrent treatment with diphenylheptane opioids, herbal medications, vitamins and other over-the-counter medications, hence the need to notify the healthcare provider on other medications in use before the administration of Lubiprostone.
• Uses: Lubiprostone is a bicyclic fatty acid metabolite analog of Prostaglandin E1. It activates specific chloride channels in the gastrointestinal tract to stimulate intestinal fluid secretion, increase gastrointestinal transit, and improve symptoms of constipation.

Technology Process of 7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid

There total 11 articles about 7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

benzyl (Z)-7-[(1R,2R,3R)-2-((E)-4,4-difluoro-3-oxo-1-octenyl)-3-(phenylmethoxy)-5-oxocyclopentyl]-5-heptenoate (1236109-40-2) → 13,14-dihydro-15-keto-16,16-difluoro-Prostaglandin E1 (136790-76-6)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethyl acetate; for 10h;

Reference yield:

(Z)-7-[(1R,2R,3R)-2-((E)-4,4-difluoro-3-oxo-1-octenyl)-3-(phenylmethoxy)-5-oxocyclopentyl]-5-heptenoic acid (1236109-29-7) → 13,14-dihydro-15-keto-16,16-difluoro-Prostaglandin E1 (136790-76-6)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In dichloromethane; for 15h; under 103.432 Torr;

Reference yield:

4-methoxybenzyl 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoro-pentyl)-octahydro-2-hydroxy-6-oxocyclopenta[b]pyran-5-yl]heptanoate → 13,14-dihydro-15-keto-16,16-difluoro-Prostaglandin E1 (136790-76-6)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; for 3h;

upstream raw materials:

benzyl (Z)-7-[(1R,2R,3R)-2-((E)-4,4-difluoro-3-oxo-1-octenyl)-3-(phenylmethoxy)-5-oxocyclopentyl]-5-heptenoate

[(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde]

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

[(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4(triisopropylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one]

Downstream raw materials:

lubiprostone

Refernces

• 1、 -. "POLYMORPHIC FORMS OF LUBIPROSTONE". . . Retrieved 2011/08/21.